


Ruby's First Anal

by Damien_Kova



Category: RWBY
Genre: Anal Sex, F/M, Sex Toys
Language: English
Status: Completed
Published: 2018-06-24
Updated: 2018-06-24
Packaged: 2019-05-27 22:23:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,000
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15034589
Author URL: https://archiveofourown.org/users/Damien_Kova/pseuds/Damien_Kova
Summary: Ruby and her boyfriend, Jaune, go through a process for Ruby’s first anal experience.





	Ruby's First Anal

Panting heavily to herself, the new couple couldn’t help but smile at each other as they laid on Ruby’s bed. The crimsonette bit her lower lip as she rolled onto her side and looked over at her lover, Jaune, gasping happily as she looked into his eyes. “Hey… You promised you were going to take all of my virginities today… There’s still one left, you know…” The silver-eyed girl licked her lips as she waited for her partner’s response, wondering if he was going to tell her to wait for a few hours. “I’ve got a dildo with me if you don’t think you’ll fit…”

 

“No no, it’s fine, Ruby. But I’ve cum inside of you four times already today. I have stamina, but I’d rather not fuck until we’re both raw.” The blue-eyed student sat up on the bed and smiled, getting out of the bed and heading toward the counter at the edge of the room. “But, if you really want it that bad right now, we’ll start slow. Sound fair?” Opening one of the drawers, Jaune smiled and nodded as he found a bottle of lube, pulling it out and making his way back to the bed. “Alright. Get on your stomach and lift your cute little ass in the air as high as you can.~”   
  
Ruby pouted as her ass was called small, pursing her lips and doing as instructed with a disgruntled huff. “It’s not small, Jaune… Take it back.”  A soft gasp left the girl’s lips as she felt a slightly cool liquid pour into the cleft of her rear end, groaning quietly as her boyfriend’s finger found its home between her ass cheeks. “J-Jaune… What are you doing…? It feels weird…” Of course, her question was answered the moment she felt her lover’s index finger begin to circle her asshole, spreading the lube around it and making her whine in response to the odd but slightly blissful sensation. However, a moment later, that whine turned into a noise of discomfort when that same finger pushed into her hole, only moving in to the second knuckle. “I thought you said this was supposed to feel good!”   
  
“It will, Ruby… Just be patient.” The young blonde leaned forward and placed a soft kiss onto the crimsonette’s cheek before slowly starting to pump his finger in and out of her, spreading what he could of the lube around. “I just need to make sure that you have plenty of lube inside of you while getting you used to having something inside of your ass.” Jaune licked his lips as he pulled his finger out of her and spread some more lube around her tight back door, a smile on his face as he pushed it back in, earning another soft whine from his girlfriend. “Does it really feel that bad, Ruby? I thought you wanted this, after all.~”   
  
“Q-Quiet, Jaune… I do want it, but it feels weird having something so small inside of me compared to your dick…” Ruby was quickly given the answer to her problem as a second finger slipped inside of her with the first and started moving in an opposite motion right away, causing the girl to bite down on the sheets to avoid letting out the mixture of slight pain and pleasure that she was feeling. It was an odd feeling having something like this in her ass, especially compared to how wonderful it felt to have Jaune’s massive cock inside of her pussy and buried into her throat. It was almost as if she was getting a downgrade from earlier, until she felt his fingers separate inside of her and spread her anal walls as much as his fingers could do without harming her. “Ah, Jaune!~” The silver-eyed girl pouted a bit as she turned her head back to see her boyfriend staring at her ass like it was the best thing in the world for him right now, as if fingering her was enough for him. Opening her mouth to shout at him and tell him to hurry and fuck her, the crimsonette was quickly silenced with a happy and loving kiss being placed on her lips.

 

“Don’t be so impatient, Ruby. I can tell when you’re upset with me by the look in your eyes.~” Jaune used his free hand to lightly tap the young girl’s nose, earning another huff before a soft moan slipped from her lips. “There we go. That’s the sound I needed to hear before I kept going. No need to do something you’re going to hate, after all.~” Slowly pulling his fingers out of her tight hole and giving her ass a good slap, chuckling as he watched it jiggle from that. “Now, where is your dildo? That’s next on the list to make sure your body is ready to take my cock.”   
  
“Under the dresser beside the window.” Ruby stuck her tongue out and gently rubbed her ass as she watched her boyfriend leave the bed and head where she told him, surprised that this was as easy and simple as it was so far. “It’s not exactly as big as you are, but I never wanted something that would risk being noticed by the others…” The crimsonette could feel a soft warmth coming to her cheeks as the blonde reached under the dresser and found a small box, pulling it out and opening it to see a six inch long and three inch wide dildo with a fake set of balls at the bottom of it. Once again, she opened her mouth to say something, only to fall silent when she saw Jaune slip the box back in its place but bring the dildo to her.   
  
“Well, this should definitely be a good start to make sure your ass is ready. Honestly, we should’ve done this with your cunt if you had it.” The boy chuckled as he sat back on the bed and crawled up behind his lover’s perky rear end, pressing the tip of the fake shaft against her puckered back door. “Oh!” Before putting it in, Jaune reached out and grabbed the lube he had left on the bed, pouring a small amount of it on the dildo since there should still be some in the crimsonette’s asshole still. “That’s much better, isn’t it?~” Of course, he didn’t know what it was like to have a dildo or a cock inside of him, but that didn’t stop him from slowly pushing the faux cock forward and forcing the first few inches into the young girl’s rear end. The young blonde couldn’t help but smile and relish in the quiet and needy moan that left the silver-eyed girl as a result of half of the fake cock pushing into her hole and stretching her a bit. Though, that didn’t stop him from keeping it still in order to not hurt her from the sudden size difference of two fingers to a three inch wide cock. “How’s it feel, Ruby?”   
  
“M-More…” Clenching onto the sheets as hard as she could, the crimsonette softly panted as her face was flush with both embarrassment and need. It felt so good having something inside of her ass, especially once Jaune began to move the dildo in and out of her, slowly pushing more and more of it into her to make sure that she slowly got used to having all of it inside of her. Before she knew it, more than likely from her mind being in a slight daze from the sudden onslaught of pleasure, the silver-eyed girl could feel the fake balls pressing against her thighs as she squeezed them together. “I-Is that all… Of it…?” Ruby couldn’t believe that she already had all of the dildo inside of her asshole, even if she could still feel a small twinge of pain shoot through her when Jaune twisted it inside of her, almost as if he was trying to tease her more than anything. “J-Jaune!”

 

“Sorry, sorry.~” The blonde boy stuck his tongue out and gently slapped his girlfriend’s ass once again, making sure it jiggled around the faux cock that he kept inside of her. “But, it feels good, doesn’t it? Having something like this inside of you.” Of course, he knew the answer to that from the slightly needy and desperate moan that left the crimsonette as he started to pull the toy out of her. “It’s okay to say that it feels good. Who knows, maybe I’ll keep going with it for awhile if you do.~” Licking his lips, the young boy pushed the toy back inside of Ruby, making her gasp and whine, squirming against the bed as he began moving the toy in and out of her like he was with his fingers a moment ago.   
  
“Please… Please don’t tease me, Jaune... I want your cock, not a toy!” Ruby turned her head and whimpered as she faced her boyfriend, a lustful and wanting look in her eyes. However, she learned rather quickly just who was in charge of what was happening when her boyfriend started to pump the toy back and forth inside of her at a much faster rate, forcing loud and needy whines from her lips as she pushed her face against the bed again, wanting to try and retain control of herself instead of begging for her lover to fuck her. Over and over again, with each and every push of the faux cock, the young girl let out another pleasured noise, all of it getting to both her head and Jaune’s.

 

“If you’re able to feel this good just from a toy, I wonder how loud I can make you scream with my cock.~” The blonde continued to move the toy in and out of the crimsonette, actually wanting to make sure that her rear end was used to receiving rapid and slightly harsh thrusts before he took to fucking it, wanting Ruby to feel as good as she possibly could when the time came. Though, that didn’t stop him from enjoying the cute and lovely sounds that left his girlfriend in the process, chuckling as he slapped her ass again and watched it jiggle in response. “Just a little bit more, Ruby. Do you think you can hold out a little longer?”

 

In truth, the silver-eyed girl had no idea, already feeling an orgasm starting to bubble up inside of her from the pressure of having her anus toyed with. Biting the sheets and trying to keep herself quiet, her mind was focused on making sure she didn’t get off before she finally got to feel her boyfriend’s thick cock in her ass. She wanted her first anal orgasm to be because of his cock, after all. Taking a deep breath and letting go of the bed, the crimsonette looked over to the blue-eyed boy and nodded, smiling cutely as she did in hopes that it would entice him to actually fuck her already and not keep her waiting.

 

Luckily, that’s exactly what it did. Jaune couldn’t help but return the loving smile he saw before slowly pulling the toy out of Ruby’s plump ass, silently relishing in her whine when she was left empty. “Alright, I ‘d say I’m satisfied and I think your ass can take it.~” The blonde adjusted himself to get on his knees behind his girlfriend and place his hands on her hips, pulling her close enough to push the tip of his cock inside of her. The couple both moaned out in unison from the pleasure before the boy pushed forward, slowly making sure that each and every inch of his cock was pushed inside of the silver-eyed girl. “Gods, it’s still so tight, Ruby. Maybe you need to get a bigger toy.~” Of course, the blue-eyed student wasn’t exactly complaining as he loved the feeling of his lover’s tight and still lubed asshole clenching down around his shaft for dear life, knowing this was going to feel amazing once he reached the base.

 

On the other hand, Ruby was in heaven as she finally felt her boyfriend’s cock in her ass, screaming in joy into the bed as she reached her hands back to spread her supple ass cheeks. “You’re so big, Jaune… It feel so good!~” The crimsonette smiled as she spanked herself, gasping as that simultaneously prompting her lover to start moving his hips back and forth inside of her. However, what felt the best was when the blonde grabbed her wrists and kept them behind her back, leaving her with nothing to support herself and force her to keep her head firmly pressed against the bed. An incoherent noise left the girl as she closed her eyes and gave into the pleasure, feeling her arousal drain down her thighs from the previous teasing. “Fuck me, Jaune! Fuck me as hard and as fast as you want.~”

 

There was no way on Remnant that the boy was possibly going to ignore that request, keeping the girl’s wrists firmly in his grip as he picked up both the pace and the harshness of his thrusts. Each and every thrust was now just as fast and rough as it was when he took her vaginal virginity, his hips almost a blur from the speed and the sound of skin slapping together filling the room from the roughness. Luckily, Ruby wasn’t the type to bruise easily and he was happy to have that knowledge in the back of his mind, continuing to pound away into the tight asshole just as fast and as hard as he wanted to. However, he let go of one of the crimsonette’s hands after a moment, using his now free hand to spank the small girl and play with her supple ass cheek while he could. “Your ass feels incredible, Ruby… This definitely won’t be the last time that I fuck it.~”   
  


“Good! Good! I want more of it! I want every inch of your fat dick inside my ass, Jaune!~” Ruby had lost it at this point, her tongue hanging out of her mouth as her body shook and swayed with each thrust into her. It didn’t matter to her how dirty it seemed to be telling someone to fuck her ass, or the chances she could get caught without trying to be quiet. All the silver-eyed girl wanted was to feel her boyfriend’s hot seed pumping into her ass as quick and as far as she could get it. Fortunately, due to the familiar feeling of Jaune’s cock throbbing inside of her tight ass, the crimsonette knew that it wouldn’t be long until she got what she wanted and could say that her man had taken all of her virginities.

 

Jaune knew he was going to cum soon, especially when the girl’s anal walls got even tighter around his shaft once he could feel himself getting close. Cumming from a blowjob, and then creampieing Ruby’s incredible pussy, and now getting to fuck her ass all in a single session was having its toll on the boy. But, here he was, holding tightly to his girlfriend’s hips and pounding away at her rear end like there was no end to his lust for her. It made him happy to know that she was getting just as needy for his cock as he was for this day, making him smile and lean forward, wrapping an arm around her body and grabbing one of her budding breasts. “I’m going to cum, Ruby!”   
  
“Do it! Cum inside me, Jaune! Cum in my ass and fill me with every drop!~” Ruby loved the feeling of the blonde’s hands on her breasts, always being slightly self-conscious about them with a sister like Yang. But when Jaune grabbed them and played with them, it had to have been one of the most blissful experiences of her life, especially with the added feeling of her ass being fucked. The crimsonette could feel her climax getting closer and closer with each thrust, the pleasure and ecstasy from the experience catching up to her as she screamed out in pure joy. The silver-eyed girl came first, throwing her head back and letting her noises fill the room around them as her anal walls clamped down around her boyfriend’s cock.

 

Of course, Jaune was right behind her with a display like that. The feeling of Ruby’s anal walls squeezing his shaft and attempting to milk it for all it was worth was a wonderful feeling, moaning and gripping tightly onto the girl’s waist in order to bury his shaft as deep into her asshole as he could manage. Rope after thick rope of cum left him and flooded the girl’s tight hole, making her squirm and writhe under him, more noises leaving her as a clear liquid splashed against the bed between them. Though, the blonde didn’t realize that his girlfriend has just squirted from behind fucked in the ass until she fell forward and slumped against the bed on her stomach, her legs shaking a bit as she laid there. “Ruby…?”

 

The young girl rolled over onto her back and smiled as she held her hand out toward Jaune, as if silently asking him to come close and get a kiss. Everything felt far too good, far better than she could’ve wanted or expected. But that didn’t stop her from smiling as the blonde came in close and she was able to pull him into a loving and passionate kiss. “That was incredible, Jaune… Thank you for taking my virginity today.” There was a pause as she spoke and looked into his blue eyes, like she was trying to find the courage to speak up. “... I love you, Jaune…”   
  
“I love you too, Ruby.” A soft smile came to the blonde’s lips as he cuddled up to the crimsonette and held her close, keeping her in his arms and letting her head rest against his chest.


End file.
